Triazine derivative and a herbicide comprising the same as an effective ingredient

ABSTRACT

The present invention relates to a novel triazine derivative represented by the general formula ##STR1## in the formula, A denotes ##STR2## (in which Y 1  denotes a hydrogen atom or a methyl group and Z denotes an oxygen atom or a sulfur atom), ##STR3## (in which Y 2  and Y 3 , which can be of the same kind or different kinds, each denote a methyl group or a methoxy group) or ##STR4## (in which Y 4  denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 ro 2), X 1  denotes a halogen atom and R 1  denotes hydrogen, a methyl group or an ethyl group as well as a herbicide containing the triazine derivative represented by the general formula (I) as an effective ingredient.

FIELD OF TECHNOLOGY

The present invention relates to novel triazine derivatives and a herbicide containing the derivatives as an effective ingredient.

1. Background Technology

A variety of herbicides have been hitherto developed and contributed to the productivity and labor-saving in agriculture. However, certain kinds of herbicides have been used over so long years that population of troublesome weeds withstanding them are increasing so that appearance is desired of a herbicids having a broad herbicidal spectrum and effectiveness also against these troublesome weeds. It is also desired to develop a high-activity herbicide in order to overcome the problem of environmental pollution by conventional herbicides. In order to overcome to the problem of the ununiform germination of weeds over a long period of time, furthermore, appearance is also awaited of a herbicide exhibiting excellent persistent effectiveness and having a versatility of treatment to exhibit effectiveness even by treatment over a wide range of period from the pregermination stage to the growing period of weeds.

The inventors have continued investigations to develop a herbicide capable of exhibiting an excellent herbicidal effect against various kinds of annual and perennial weeds without causing phytotoxicity to paddy rice and arrived at a discovery that a herbicide containing a triazine compound as an effective ingredient is effective (official publication of Japanese Patent Toku-sai-hyo 88/02368, official publication of Japanese Patent Kokai 63-146876, official publication of Japanese Patent Kokai 63-51379 and official publication of Japanese Patent Kokai 63-264465). This triazine-based herbicide is highly active against troublesome weeds in paddy rice field at low dosage without phytotoxicity to paddy rice plant. This herbicide also shows excellent herbicidal activity against troublesome weeds by foliage application in upland field without phytotoxicity to Gramineous crops.

Nevertheless, this herbicide shows somewhat limited performance by preemergence treatment to the soil in upland fields.

2. Disclosure Of The Invention

The present invention provides:

(1) a triazine derivative represented by the general formula ##STR5## in the formula, A denotes ##STR6## (in which Y¹ denotes a hydrogen atom or a methyl group and Z denotes an oxygen atom or a sulfur atom), ##STR7## (in which Y² and Y³, which can be of the same kind or different kinds, each denote a methyl group or a methoxy group) or ##STR8## (in which Y⁴ denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X¹ denotes a halogen atom and R¹ denotes hydrogen, a methyl group or an ethyl group , and

(2) a herbicide containing, as an effective ingredient, a triazine derivative represented by the general formula ##STR9## in the formula, A denotes ##STR10## in which Y¹ denotes a hydrogen atom or a methyl group and Z denotes an oxygen atom or a sulfur atom), ##STR11## (in which Y² and Y³, which can be of the same kind or different kinds, each denote a methyl group or a methoxy group) or ##STR12## (in which Y⁴ denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X¹ denotes a halogen atom and R¹ denotes hydrogen, a methyl group or an ethyl group.

The inventors have continued investigations to search a compound free from phytotoxicity to the crops of the family of Gramineae in upland fields capable of exhibiting a high herbicidal effect against troublesome weeds both in the treatment to soil and in the treatment to foliage with an excellent effect of soil treatment in paddy fields. As a result, a discovery has been reached that those having a specific haloalkyl group are effective leading to completion of the present invention.

The triazine derivative of the present invention is a novel compound and can be effectively utilized as a herbicide. When used as a herbicide for upland fields, the herbicide of the present invention containing the triazine derivative as an effective ingredient can be used over a long term for appropriate chemical treatment as compared with existing herbicides for upland fields and exhibits a high activity against troublesome weeds both in the soil treatment before germination and in the course of germination of the weeds and in the foliage treatment during the growth period of the weeds still without phytotoxicity to crops. In particular, a remarkably high effect is obtained by the soil treatment or treatment to foliage in non-paddy fields of crops belonging to Gramineous crops. As compared with existing herbicides for paddy rice, in addition, the herbicide of the present invention has a high chemical effect against hardly eliminable weeds still with little phytotoxicity.

BEST MODE TO PRACTICE THE INVENTION

The present invention provides a triazine derivative represented by the general formula ##STR13## in the formula, A denotes ##STR14## (in which Y¹ denotes a hydrogen atoms or a methyl group and Z denotes an oxygen atom or a sulfur atom), Y³ ##STR15## (in which Y² and Y³, which can be of the same kind or of different kinds, each denote a methyl group or a methoxy group) or ##STR16## (in which Y⁴ denotes a methyl group, trifluoromethyl group, methoxy group or fluorine atom and n denotes an integer of 0 to 2), X¹ denotes a halogen atom and R¹ denotes hydrogen, a methyl group or an ethyl group and also provides a herbicide containing the triazine derivative represented by the above given general formula [I].

The triazine derivative of the present invention represented by the above given general formula [I] can be prepared by various different methods. The method of preparation with the highest efficiency among them is the method to react an alkyl amine salt represented by the general formula ##STR17## in the formula, A is the same as given above and X³ denotes a halogen atom and cyanoguanidine expressed by the formula ##STR18## to prepare an alkyl biguanide salt represented by the general formula ##STR19## in the formula, A and X³ are each the same as given above] and then to react the alkyl biguanide salt with an alkyl ester represented by the general formula ##STR20## in the formula, R¹ and X¹ are each the same as given above and R² denotes an alkyl group having 1 to 4 carbon atoms . In this manner, the alkyl amine salt represented by the general formula [II] and cyanoguanidine are reacted to give the alkyl biguanide salt represented by the general formula [III] which is reacted with the alkyl ester represented by the general formula [IV] to give the desired triazine derivative represented by the general formula [I] in high efficiency.

In conducting the reaction between the alkyl amine salt represented by the above given general formula [II] and cyanoguanidine here, these two compounds can be used in an approximately equimolar proportion and usable solvents include cyclic hydrocarbons such as benzene, Decalin, alkyl naphthalenes and the like and chlorinated hydrocarbons such as carbon tetrachloride, ethylene dichloride, chlorobenzene, dichlorobenzene, trichlorobenzene and the like. And, the reaction temperature is not particularly limitative and sufficient proceeding can be obtained in the range from low to high temperatures or, in particular, from 80° to 200° C.

The salt of an alkyl biguanide derivative represented by the general formula [III] is obtained by this reaction and, in the method of the present invention, this is reacted with the alkyl ester of the general formula [IV] ##STR21## to prepare the desired triazine derivative represented by the general formula [I]. This reaction usually proceeds in high efficiency at about 10° to 100° C. in the presence of a catalyst such as a base and the like in a solvent such as alcohols, e.g., methanol, ethanol, isopropanol and the like, various kinds of ketones, aliphatic hydrocarbons, various kinds of ethers, various kinds of cyclic hydrocarbons, chlorinated hydrocarbons and the like.

The triazine derivatives of the general formula [I] obtained by the above described method are novel compounds.

And, the compound of the present invention has optical isomers and is obtained usually as a racemic modification while it is possible to obtain the respective antipodes by a known method such as asymmetric synthesis. The compound of the present invention can be used as a herbicide either in the form of the racemic modification or in the form of the isolated optical isomer. Furthermore, the compound of the present invention also can be used as a herbicide in the form of a salt of an inorganic acid or organic acid.

Furthermore, the triazine derivative represented by the general formula [I] inhibits germination and growth of weeds and has high selectivity so that it is satisfactory as a herbicide. In addition, it is useful not only for the soil treatment before the germination of weeds as a matter of course but also for the foliage treatment to the growing weeds to have a versatility of the chemical treatment. The triazine derivative of the present invention exhibits no phytotoxicity to the crops belonging to Gramineous crops such as corn, grain sorghum, wheat, barley, oat and the like as the important crops in upland fields and exhibits a prominent herbicidal effect against strongly troublesome broadleaf weeds such as Cassia obtusifolia L., Ipomoea purpurea, Abutilon theophrasti, Galium sparium var. echinospermon, Stellaria media, Veronica persica, Polygonum persicaria, Viola arvensis, Brassica juncea, Amaranthus patulus, Common blackjack and the like and strongly harmful weeds belonging to the family of Graminea such as Digitaria sanguinalis, Alopecurus myosuroides and the like.

Furthermore, this triazine derivative not only exhibits a prominent herbicidal effect against broadleaf weeds such as Rotala indica (Willd) Koehne var. uligirosa (Miq.) Koehne, Lindernia pyxidaria L., Monochoria vaginalis Presl var. plantaginea and the like, weeds belonging to the family of Cyperaceae such as Cyperus difformis L. and the like and weeds belonging to the family of Gramineae such as Echinochloa crus-galli P. Beauv. var. formosensis Ohwi and the like but also exhibits a prominent herbicidal effect against perennial weeds such as Scirpus juncoides Roxb. ssp. Hotarui Ohwi T. Koyama, Cyperus serotinus Rottb., Sagittaria pygmaea Miq. and the like, which are currently deemed to be hardly eliminable, without causing chemical damages against paddy rice.

In the next place, the herbicide of the present invention contains the above described compound or, namely, the triazine derivative represented by the general formula [I] as the effective ingredient and these compounds can be used as being prepared in the preparation form such as a water-dispersible powder, emulsion, dust, granules, flowable agent, solution and the like by mixing with a liquid carrier such as solvents and the like or a solid carrier such as mineral fine powders and the like. In the preparation of the form, it is optional according to need to add an emulsifying agent, dispersion aid, spreading agent, suspending agent, penetrating agent, stabilizer and other adjuvants.

When the herbicide of the present invention is used in the form of a water-dispersible powder, usually, a composition to be used is prepared by compounding from 10 to 55% by weight of the above described triazine derivative of the present invention as the effective ingredient, from 40 to 88% by weight of a solid carried and from 2 to 5% by weight of a surface active agent. Further, when it is used in the form of an emulsion or a flowable agent, it can be usually prepared by compounding from 5 to 50% by weight of the triazine derivative of the present invention as the effective ingredient, from 35 to 90% by weight of a solvent and a surface active agent and from to 15% by weight of other adjuvants.

When it is used in the form of a dust, on the other hand, it can be prepared usually by compounding from 1 to 15% by weight of the triazine derivative of the present invention as the effective ingredient and from 85 to 99% by weight of a solid carrier. When it is used in the form of granules, furthermore, they can be prepared usually by compounding from 0.1 to 15% by weight of the triazine derivative of the present invention as the effective ingredient, from 80 to 97.9% by weight of a solid carrier and from 2 to 5% by weight of a surface active agent. The solid carrier used here is a fine mineral powder and such a fine mineral powder includes diatomaceous earth, oxides such as hydrated lime and the like, phosphates such as apatite and the like, sulfates such as gypsum and the like, silicates such as talc, pyrophyllite, clay, kaolin, bentonite, acid clay, white carbon, quartz powder, silica stone powder and the like, and so on.

And, the liquid carrier includes organic solvents such as paraffinic or naphthenic hydrocarbons, e.g., kerosine, mineral oil, spindle oil and the like, aromatic hydrocarbons, e.g., benzene, toluene, xylene and the like, chlorinated hydrocarbons, e.g., 2-chlorotoluene, trichloromethane, trichloroethylene and the like, alcohols, e.g., cyclohexanol, amyl alcohol, ethylene glycol and the like, alcohol ethers, e.g., ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and the like, ketones, e.g., isophorone, cyclohexanone, cyclohexenyl cyclohexanone and the like, ethers, e.g., Butyl Cellosolve, dimethyl ether, methyl ethyl ether and the like, esters, e.g., isopropyl acetate, benzyl acetate, methyl phthalate and the like, amides e.g., dimethyl formamide and the like, nitriles, e.g., acetonitrile, propionitrile and the like, and sulfoxides, e.g., dimethyl sulfoxide and the like as well as mixtures thereof, water and the like.

Further, as the surface active agent, any one can be used among the anionic type ones (alkylbenzene sulfonates, alkyl sulfonates, lauric acid amide sulfonate and the like), nonionic type ones (polyoxyethylene octyl ether, polyethylene glycol laurate, sorbitan alkyl esters and the like), cationic type ones (dimethyl lauryl benzyl ammonium chloride, lauryl amine, stearyl trimethyl ammonium chloride and the like) and amphoteric type ones (amino acids, betaine and the like).

Further, it is optional with an object to improve the nature of the preparation form and to enhance the herbicidal effect that the compound of the present invention is used in combination with a polymeric compound or adjuvant such as sodium alginate, carboxymethyl cellulose, carboxy vinyl polymer, gum arabic, hydroxypropyl methyl cellulose and the like.

The above described triazine derivative of the present invention as a novel compound represented by the general formula [I] exhibits an excellent effect as a high-selectivity herbicide not causing any phytotoxicity for the crops in nonpaddy fields such as corn, grain sorghum, wheat, barley, oat and the like by the soil treatment or foliage treatment either before germination or after germination of weeds. And, the herbicidal effect is high not only against annual weeds as a matter of course but also against perennial weeds and it is very useful as a high-selecte herbicide not causing any phytotoxicity also for paddy rice.

The herbicide of the present invention is administered in a dose of approximately from 0.1 to 1000 g or, preferably, from 1 to 100 g per 10 ares as the effective ingredient. When it is applied on foliage of plants, it is administered as being diluted to about 1 to 10000 ppm or, preferably, to 10 to 1000 ppm.

Incidentally, it is optional to use the triazine derivative represented by the general formula [I] in combination with other herbicidal constituents as the effective ingredient of the herbicide of the present invention. Such an auxiliary herbicidal constituent can be a herbicide hitherto on the market including various ones exemplified, for example, by the phenoxy-type herbicides, diphenyl ether-type herbicides, triazine-type herbicides, urea-type herbicides, carbamate-type herbicides, thiol carbamate-type herbicides, acid anilide-type herbicides, pyrazole-type herbicides, phosphoric acid-type herbicides, sulfonyl urea-type herbicides, nitrile-type herbicides, dinitroaniline-type herbicides, imidazolinone-type herbicides, oxadiazone and the like.

Furthermore, the herbicide of the present invention can be used as mixture with insecticides, germicides, growth-controlling agents of plants, fertilizers and the like according to need.

EXAMPLES

In the following, the present invention is described in further detail by way of examples.

PREPARATION EXAMPLE 1

Sodium methoxide was produced by gradually adding 0.92 g (40 m moles) of sodium to 20 ml of dried methanol and 2-(3',5'-dimethylphenoxy) isopropyl biguanide hydrochloride (20 m moles) (described in the official publication of Japanese Patent Kokai No. 63-264465) as the starting material I was added thereto and agitated for 30 minutes at room temperature. In the next place, 4.80 ml (40 m moles) of ethyl ester of α-fluoro-α-methyl propionic acid as the starting material II were added dropwise and agitated for 10 hours at room temperature. After completion of the reaction, the content material was poured into 100 ml of water and subjected to three times of extraction with 50 ml of ethyl acetate. This ethyl acetate layer was dried with anhydrous sodium sulfate followed by removal of the ethyl acetate by distillation under reduced pressure. The residue was purified by the silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) followed by recrystallization from hexane-ethyl ether to give white 2-amino-4-[2-(3',5'-dimethylphenoxy) isopropylamino]-6 -fluoroisopropyl-s-triazine (compound I). The produced amount, % yield, results of analysis, structural formula and others thereof are shown in Tables 1 to 3.

PREPARATION EXAMPLES 2 TO 41

Compounds 2 to 41 were obtained by conducting the same procedure as in Preparation Example 1 excepting the use of 20 m moles of the alkyl biguanide hydrochloride (described in the official publication of Japanese Patent Toku-Sai-Hyo No. 88/02368, official publication of Japanese Patent Kokai No. 63-51379 and official publication of Japanese Patent Kokai No. 63-264465) indicated in Table 1 in place of the 2-(3',5'-dimethylphenoxy) isopropyl biguanide hydrochloride as the starting material I in Preparation Example 1 and the use of 20 m moles of the ester indicated in Table 1 in place of the ethyl ester of α-fluoro-α-methyl propionic acid as the starting material II. The produced amounts, % yields, results of analysis, structural formulas and others of these compounds are shown in Tables 1 to 3.

                                      TABLE 1                                      __________________________________________________________________________                                          Results of Analysis (%)                   Preparation                          Melting                                                                             Elementary                           Example No.                                                                             Starting Materials  Yield                                                                              Yield                                                                              Point                                                                               Analysis (%)                         (Compound No.)                                                                          I         II        (g) (%) (°C.)                                                                        C   H   N                            __________________________________________________________________________     Preparation                                                                             2-(3',5'-dimethyl-                                                                       α-fluoro, α-methyl                                                           2.53                                                                               38  102.4-                                                                              53.9                                                                               7.3 21.0                         Example 1                                                                               phenoxy)-1-methyl-                                                                       propionic acid    104.9                                                                               (61.2)                                                                             (7.3)                                                                              (21.0)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester                                                 No. 1)                                                                         Preparation                                                                             2-(3',5'-dimethyl-                                                                       α-fluoro-propionic                                                                 0.83                                                                               13  Color-                                                                              60.0                                                                               7.1 22.3                         Example 2                                                                               phenoxy)-1-methyl-                                                                       acid n-butyl      less,                                                                               (60.2)                                                                             (6.9)                                                                              (21.9)                       (Compound                                                                               ethyl biganide                                                                           ester             resinous                                  No. 2)                                                                         Preparation                                                                             2-(3',5'-dimethyl-                                                                       α-chloro-                                                                          1.61                                                                               24  Color-                                                                              56.2                                                                               6.7 21.2                         Example 3                                                                               phenoxy)-1-methyl-                                                                       propionic acid    less,                                                                               (57.2)                                                                             (6.6)                                                                              (20.9)                       (Compound                                                                               ethyl biganide                                                                           methyl ester      resinous                                  No. 3)                                                                         Preparation                                                                             2-(2',5'-dimethyl-                                                                       α-fluoro, α-methyl                                                           2.80                                                                               42  134.5-                                                                              60.9                                                                               7.1 21.2                         Example 4                                                                               phenoxy)-1-methyl-                                                                       propionic acid    136.0                                                                               (61.2)                                                                             (7.3)                                                                              (21.0)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester                                                 No. 4)                                                                         Preparation                                                                             2-(2',3'-dimethyl-                                                                       α-fluoro, α -methyl                                                          2.27                                                                               34  Color-                                                                              63.0                                                                               7.4 21.1                         Example 5                                                                               phenoxy)-1-methyl-                                                                       propionic acid    less,                                                                               (61.2)                                                                             (7.3)                                                                              (21.0)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 5)                                                                         Preparation                                                                             2-(2',5'-dimethyl-                                                                       α-chloro, α-methyl                                                           1.06                                                                               15  Color-                                                                              59.0                                                                               6.7 20.4                         Example 6                                                                               phenoxy)-1-methyl-                                                                       propionic acid    less,                                                                               (58.4)                                                                             (6.9)                                                                              (20.0)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 6)                                                                         Preparation                                                                             2-(2',3'-dimethyl-                                                                       α-chloro, α-methyl                                                           0.82                                                                               12  Color-                                                                              58.0                                                                               7.2 19.6                         Example 7                                                                               phenoxy)-1-methyl-                                                                       propionic acid    less,                                                                               (58.4)                                                                             (6.9)                                                                              (20.0)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 7)                                                                         Preparation                                                                             2-(2',3'-dimethyl-                                                                       α-fluoro-propionic                                                                 0.48                                                                                8  Color-                                                                              60.0                                                                               6.9 22.3                         Example 8                                                                               phenoxy)-1-methyl-                                                                       acid n-butyl ester                                                                               less,                                                                               (60.2)                                                                             (6.9)                                                                              (21.9)                       (Compound                                                                               ethyl biganide              resinous                                  No. 8)                                                                         Preparation                                                                             2-(3',5'-dimethyl-                                                                       α-chloro, α-methyl                                                           2.01                                                                               29  Color-                                                                              57.9                                                                               7.0 20.2                         Example 9                                                                               phenoxy)-1-methyl-                                                                       propionic acid    less,                                                                               (58.4)                                                                             (6.9)                                                                              (20.0)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 9)                                                                         Preparation                                                                             2-(3',5'-dimethyl-                                                                       α-bromo, α-methyl                                                            1.85                                                                               24  Color-                                                                              52.2                                                                               6.0 17.5                         Example 10                                                                              phenoxy)-1-methyl-                                                                       propionic acid    less,                                                                               (51.8)                                                                             (6.1)                                                                              (17.8)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 10)                                                                        Preparation                                                                             2-(3'-trifluoro-                                                                         α-fluoro, α-methyl                                                           2.09                                                                               28  Color-                                                                              51.9                                                                               5.0 18.4                         Example 11                                                                              methylphenoxy)-1-                                                                        propionic acid    less,                                                                               (51.5)                                                                             (5.1)                                                                              (18.8)                       (Compound                                                                               methyl-ethyl                                                                             ethyl ester       resinous                                  No. 11)  biganide                                                              Preparation                                                                             2-(3'-methyl                                                                             α-fluoro, α-methyl                                                           1.32                                                                               21  95.3-                                                                               60.0                                                                               6.8 22.2                         Example 12                                                                              phenoxy)-1-methyl                                                                        propionic acid    97.0 (60.2)                                                                             (6.9)                                                                              (21.9)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester                                                 No. 12)                                                                        Preparation                                                                             2-(3'-methyl                                                                             α-fluoro-propionic                                                                 0.45                                                                                7  Color-                                                                              59.2                                                                               6.9 22.5                         Example 13                                                                              phenoxy)-1-methyl                                                                        acid n-butyl ester                                                                               less,                                                                               (59.0)                                                                             (6.6)                                                                              (22.9)                       (Compound                                                                               ethyl biganide              resinous                                  No. 13)                                                                        Preparation                                                                             2-(3'-trifluoro-                                                                         α-fluoro-propionic                                                                 1.09                                                                               15  Color-                                                                              50.5                                                                               4.5 19.9                         Example 14                                                                              methylphenoxy)-1-                                                                        acid n-butyl ester                                                                               less,                                                                               (50.1)                                                                             (4.8)                                                                              (19.5)                       (Compound                                                                               methyl-ethyl                resinous                                  No. 14)  biganide                                                              Preparation                                                                             2-(3'-methyl                                                                             α-chloro, α-methyl                                                           1.11                                                                               16  Color-                                                                              57.0                                                                               6.9 20.5                         Example 15                                                                              phenoxy)-1-methyl                                                                        propionic acid    less,                                                                               (57.2)                                                                             (6.6)                                                                              (20.9)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 15)                                                                        Preparation                                                                             2-phenoxy α-chloro, α-methyl                                                           1.04                                                                               16  Color-                                                                              56.4                                                                               6.1 22.0                         Example 16                                                                              1-methyl-ethyl                                                                           propionic acid    less,                                                                               (56.0)                                                                             (6.3)                                                                              (21.8)                       (Compound                                                                               biganide  ethyl ester       resinous                                  No. 16)                                                                        Preparation                                                                             2-phenoxy α-fluoro, α-methyl                                                           1.64                                                                               27  Color-                                                                              58.7                                                                               6.8 23.1                         Example 17                                                                              1-methyl-ethyl                                                                           propionic acid    less,                                                                               (59.0)                                                                             (6.6)                                                                              (22.9)                       (Compound                                                                               biganide  ethyl ester       resinous                                  No. 17)                                                                        Preparation                                                                             2-phenoxy α-fluoro-propionic                                                                 0.58                                                                               9.6 Color-                                                                              58.1                                                                               6.0 24.2                         Example 18                                                                              1-methyl-ethyl                                                                           acid n-butyl ester                                                                               less,                                                                               (57.7)                                                                             (6.1)                                                                              (24.0)                       (Compound                                                                               biganide                    resinous                                  No. 18)                                                                        Preparation                                                                             2-(3'-methoxy-                                                                           α-fluoro, α-methyl                                                           1.42                                                                               21  Color-                                                                              56.9                                                                               6.8 20.7                         Example 19                                                                              phenoxy)-1-methyl                                                                        propionic acid    less,                                                                               (57.3)                                                                             (6.6)                                                                              (20.9)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 19)                                                                        Preparation                                                                             2-(3',4'-dimethyl-                                                                       α-fluoro, α-methyl                                                           0.61                                                                               9.2 Color-                                                                              60.8                                                                               6.9 21.3                         Example 20                                                                              phenoxy)-1-methyl                                                                        propionic acid    less,                                                                               (61.2)                                                                             (7.3)                                                                              (21.0)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 20)                                                                        Preparation                                                                             2-(3'-fluoro-                                                                            α-fluoro, α-methyl                                                           3.88                                                                               60  Color-                                                                              55.9                                                                               5.6 22.0                         Example 21                                                                              phenoxy)-1-methyl                                                                        propionic acid    less,                                                                               (55.7)                                                                             (5.9)                                                                              (21.7)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 21)                                                                        Preparation                                                                             2-(2'-fluoro-                                                                            α-fluoro, α-methyl                                                           0.19                                                                               3   Color-                                                                              56.0                                                                               6.2 21.5                         Example 22                                                                              phenoxy)-1-methyl                                                                        propionic acid    less,                                                                               (55.7)                                                                             (5.9)                                                                              (21.7)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 22)                                                                        Preparation                                                                             2-(4' -fluoro-                                                                           α-fluoro, α-methyl                                                           0.84                                                                               13  Color-                                                                              55.2                                                                               5.8 21.6                         Example 23                                                                              phenoxy)-1-methyl-                                                                       propionic acid    less,                                                                               (55.7)                                                                             (5.9)                                                                              (21.7)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester       resinous                                  No. 23)                                                                        Preparation                                                                             1-(benzofuran-                                                                           α-fluoro, α-methyl                                                           4.74                                                                               75  161.5-                                                                              60.7                                                                               5.9 22.5                         Example 24                                                                              2'-yl)ethyl                                                                              propionic acid    162.4                                                                               (60.9)                                                                             (5.8)                                                                              (22.2)                       (Compound                                                                               biganide  ethyl ester                                                 No. 24)                                                                        Preparation                                                                             1-(benzofuran-                                                                           α-chloro, α-methyl                                                           5.64                                                                               85  138.8-                                                                              57.5                                                                               5.2 20.8                         Example 25                                                                              2'-yl)ethyl                                                                              propionic acid    139.7                                                                               (57.9)                                                                             (5.5)                                                                              (21.1)                       (Compound                                                                               biganide  methyl ester                                                No. 25)                                                                        Preparation                                                                             1-(benzofuran-                                                                           α-bromo, α-methyl                                                            5.56                                                                               74  149.8-                                                                              51.3                                                                               4.6 18.3                         Example 26                                                                              2'-yl)ethyl                                                                              propionic acid    150.7                                                                               (51.1)                                                                             (4.8)                                                                              (18.6)                       (Compound                                                                               biganide  ethyl ester                                                 No. 26)                                                                        Preparation                                                                             1-(benzofuran-                                                                           α-fluoro-propionic                                                                 2.84                                                                               47  139.0-                                                                              59.6                                                                               5.1 23.5                         Example 27                                                                              2'-yl)ethyl                                                                              acid ethyl ester  140.2                                                                               (59.8)                                                                             (5.4)                                                                              (23.2)                       (Compound                                                                               biganide                                                              No. 27)                                                                        Preparation                                                                             1-(benzofuran-                                                                           α-chloro-propionic                                                                 5.02                                                                               79  145.3-                                                                              56.5                                                                               5.3 22.3                         Example 28                                                                              2'-yl)ethyl                                                                              acid methyl ester 147.4                                                                               (56.7)                                                                             (5.1)                                                                              (22.0)                       (Compound                                                                               biganide                                                              No. 28)                                                                        Preparation                                                                             1-(benzofuran-                                                                           α-fluoro, α-methyl                                                           3.20                                                                               48  153.9-                                                                              62.2                                                                               6.4 21.1                         Example 29                                                                              2'-yl)ethyl                                                                              butyric acid      155.2                                                                               (62.0)                                                                             (6.1)                                                                              (21.3)                       (Compound                                                                               biganide  ethyl ester                                                 No. 29)                                                                        Preparation                                                                             1-(benzothiophen-                                                                        α-fluoro, α-methyl                                                           4.76                                                                               72  134.2-                                                                              58.2                                                                               5.3 20.9                         Example 30                                                                              2'-yl)ethyl                                                                              propionic acid    136.0                                                                               (58.0)                                                                             (5.5)                                                                              (21.1)                       (Compound                                                                               biganide  ethyl ester                                                 No. 30)                                                                        Preparation                                                                             1-(benzothiophen-                                                                        α-chloro, α-methyl                                                           4.86                                                                               70  Color-                                                                              55.0                                                                               5.4 20.3                         Example 31                                                                              2'-yl)ethyl                                                                              propionic acid    less,                                                                               (55.2)                                                                             (5.2)                                                                              (20.1)                       (Compound                                                                               biganide  methyl ester      resinous                                  No. 31)                                                                        Preparation                                                                             1-(benzothiophen-                                                                        α-fluoro-propionic                                                                 2.28                                                                               36  Color-                                                                              57.0                                                                               4.9 22.5                         Example 32                                                                              2'-yl)ethyl                                                                              acid ethyl ester  less,                                                                               (56.8)                                                                             (5.1)                                                                              (22.1)                       (Compound                                                                               biganide                    resinous                                  No. 32)                                                                        Preparation                                                                             1-(6'-methyl-                                                                            α-fluoro, α-methyl                                                           5.54                                                                               84  168.5-                                                                              62.4                                                                               6.0 21.1                         Example 33                                                                              benzofuran-2'-yl)                                                                        propionic acid    169.3                                                                               (62.0)                                                                             (6.1)                                                                              (21.3)                       (Compound                                                                               ethyl biganide                                                                           ethyl ester                                                 No. 33)  hydrochloride                                                         Preparation                                                                             1-(6'-methyl-                                                                            α-fluoro-propionic                                                                 3.28                                                                               52  Color-                                                                              61.2                                                                               5.6 22.0                         Example 34                                                                              benzofuran-2'-yl)                                                                        acid ethyl ester  less,                                                                               (60.9)                                                                             (5.8)                                                                              (22.2)                       (Compound                                                                               ethyl biganide              resinous                                  No. 34)  hydrochloride                                                         Preparation                                                                             1-(6'-methyl-                                                                            α-chloro, α-methyl                                                           5.18                                                                               75  Color-                                                                              58.7                                                                               5.8 20.4                         Example 35                                                                              benzofuran-2'-yl)                                                                        propionic acid    less,                                                                               (59.0)                                                                             (5.8)                                                                              (20.3)                       (Compound                                                                               ethyl biganide                                                                           methyl ester      resinous                                  No. 35)  hydrochloride                                                         Preparation                                                                             2-(3'-methoxy, 4'-                                                                       α-fluoro, α-methyl                                                           2.17                                                                               34  115.1-                                                                              58.7                                                                               6.7 21.6                         Example 36                                                                              methylphenyl)-1-                                                                         propionic acid    116.8                                                                               (60.2)                                                                             (6.9)                                                                              (21.9)                       (Compound                                                                               methyl-ethyl                                                                             ethyl ester                                                 No. 36)  biganide                                                                       hydrochloride                                                         Preparation                                                                             2-(3'-methoxy, 4'-                                                                       α-fluoro-propionic                                                                 1.34                                                                               22  Color-                                                                              57.3                                                                               6.5 22.8                         Example 37                                                                              methylphenyl)-1-                                                                         acid n-butyl ester                                                                               less,                                                                               (59.0)                                                                             (6.6)                                                                              (22.9)                       (Compound                                                                               methyl-ethyl                resinous                                  No. 37)  biganide                                                                       hydrochloride                                                         Preparation                                                                             2-(3'-methoxy, 4'-                                                                       α-chloro, α-methyl                                                           2.42                                                                               36  Color-                                                                              57.4                                                                               6.7 20.6                         Example 38                                                                              methylphenyl)-1-                                                                         propionic acid    less,                                                                               (57.2)                                                                             (6.6)                                                                              (20.9)                       (Compound                                                                               methyl-ethyl                                                                             ethyl ester       resinous                                  No. 38)  biganide                                                                       hydrochloride                                                         Preparation                                                                             2-(3'-methyl, 4'-                                                                        α-fluoro, α-methyl                                                           1.98                                                                               31  Color-                                                                              60.3                                                                               6.8 22.2                         Example 39                                                                              methylphenyl)-1-                                                                         propionic acid    less,                                                                               (60.2)                                                                             (6.9)                                                                              (21.9)                       (Compound                                                                               methyl-ethyl                                                                             ethyl ester       resinous                                  No. 39)  biganide                                                                       hydrochloride                                                         Preparation                                                                             2-(3'-methyl, 4'-                                                                        α-fluoro-propionic                                                                 1.22                                                                               20  Color-                                                                              59.1                                                                               6.9 22.7                         Example 40                                                                              methylphenyl)-1-                                                                         acid n-butyl ester                                                                               less,                                                                               (59.0)                                                                             (6.6)                                                                              (22.9)                       (Compound                                                                               methyl-ethyl                resinous                                  No. 40)  biganide                                                                       hydrochloride                                                         Preparation                                                                             2-(3'-methyl, 4'-                                                                        α-chloro, α-methyl                                                           2.22                                                                               33  Color-                                                                              57.0                                                                               6.8 21.0                         Example 41                                                                              methylphenyl)-1-                                                                         propionic acid    less,                                                                               (57.2)                                                                             (6.6)                                                                              (20.9)                       (Compound                                                                               methyl-ethyl                                                                             ethyl ester       resinous                                  No. 41)  biganide                                                                       hydrochloride                                                         __________________________________________________________________________      *The value in the brackets shows the theoretical value.                  

                                      TABLE 2                                      __________________________________________________________________________                                         Molecular weight                                                               of triazine                                No.    Structural formula of triazine derivative                                                                   derivative                                                                               Triazine derivative              __________________________________________________________________________     Prepara- tion Example 1                                                                ##STR22##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                       2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   3',5'-dimethyl- phenoxy)-1-m                                                   ethyl-ethylamino]- s-triazin                                                   e                                Prepara- tion Example 2                                                                ##STR23##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                       2-amino-4-(α-fluoroeth                                                   yl)-6- [2-(3',5'-dimethylphe                                                   noxy)- 1-methyl-ethylamino]-                                                   s-triazine                       Prepara- tion Example 3                                                                ##STR24##                   C.sub.16 H.sub.22 N.sub.5 OCl                                                            2-amino-4-(α-chloroeth                                                   yl)-6- [2-(3',5'-dimethylphe                                                   noxy)-1- methyl-ethylamino]-                                                   s-triazine                       Prepara- tion Example 4                                                                ##STR25##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                       2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   2',3'-dimethyl- phenoxy)-1-m                                                   ethyl-ethylamino]- s-triazin                                                   e                                Prepara- tion Example 5                                                                ##STR26##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                       2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   2',5'-dimethyl- phenoxy)-1-m                                                   ethyl-ethylamino]- s-triazin                                                   e                                Prepara- tion Example 6                                                                ##STR27##                   C.sub.17 H.sub.24 N.sub.5 OCl                                                            2-amino-4-(α-chloro,                                                     α-methyl ethyl)-6-[2-(                                                   2',5'-dimethyl phenoxy)-1-me                                                   thyl-ethylamino]- s-triazine     Prepara- tion Example 7                                                                ##STR28##                   C.sub.17 H.sub.24 N.sub.5 OCl                                                            2-amino-4-(α-chloro,                                                     α-methyl ethyl)-6-[2-(                                                   2',3'-dimethyl- phenoxy)-1-m                                                   ethyl-ethylamino]- s-triazin                                                   e                                Prepara- tion Example 8                                                                ##STR29##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                       2-amino-4-(α-fluoroeth                                                   yl)-6- [2-(2',3'-dimethylphe                                                   noxy)- 1-methyl-ethylamino]-                                                   s-triazine                       Prepara- tion Example 9                                                                ##STR30##                   C.sub.17 H.sub.24 N.sub.5 OCl                                                            2-amino-4-(α-chloro,                                                     α-methyl ethyl)-6-[2-(                                                   3',5'-dimethyl- phenoxy)-1-m                                                   ethyl-ethylamino]- s-triazin                                                   e                                Prepara- tion Example 10                                                               ##STR31##                   C.sub.17 H.sub.24 N.sub.5 OBr                                                            2-amino-4-(α-bromo,                                                      α-methyl ethyl)-6-[2-(                                                   3',5'-dimethyl- phenoxy)-1-m                                                   ethyl-ethylamino]- s-triazin                                                   e                                Prepara- tion Example 11                                                               ##STR32##                   C.sub.16 H.sub.19 N.sub.5 OF.sub.4                                             373.4     2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   2',3'-trifluoro- methylpheno                                                   xy)-1-methyl-ethyl-                                                            amino]-s-triazine                Prepara- tion Example 12                                                               ##STR33##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                       2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   3'-methylphenoxy)-1-                                                           methyl-ethylamino]-s-triazin                                                   e                                Prepara- tion Example 13                                                               ##STR34##                   C.sub.15 H.sub.20 N.sub.5 OF 305.4                                                       2-amino-4-(α-fluoroeth                                                   yl)-6- [2-(3'-methylphenoxy)                                                   -1- methyl-ethylamino]-s-tri                                                   azine                            Prepara- tion Example 14                                                               ##STR35##                   C.sub.15 H.sub.17 N.sub.5 OF.sub.4                                             359.3     2-amino-4-(α-fluoroeth                                                   yl)-6- [2-(3'-trifluoromethy                                                   lphenoxy)- 1-methyl-ethylami                                                   no]-s-triazine                   Prepara- tion Example 15                                                               ##STR36##                   C.sub.16 H.sub.22 N.sub.5 Cl 335.8                                                       2-amino-4-(α-chloro,                                                     α-methyl ethyl)-6-[2-(                                                   3'-methylphenoxy)- 1-methyl-                                                   ethylamino]-s-triazine           Prepara- tion Example 16                                                               ##STR37##                   C.sub.15 H.sub.20 N.sub.5 OCl                                                            2-amino-4-(α-chloro,                                                     α-methyl ethyl)-6-(2-p                                                   henoxy-1-methyl- ethylamino)                                                   -s-triazine                      Prepara- tion Example 17                                                               ##STR38##                   C.sub.15 H.sub.20 N.sub.5 OF 321.8                                                       2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-(2-p                                                   henoxy-1-methyl- ethylamino)                                                   -s-triazine                      Prepara- tion Example 18                                                               ##STR39##                   C.sub.14 H.sub.18 N.sub.5 OF 291.3                                                       2-amino-4-(α-fluoroeth                                                   yl)-6- (2-phenoxy-1-methyl-e                                                   thylamino)- s-triazine           Prepara- tion Example 19                                                               ##STR40##                   C.sub.16 H.sub.22 N.sub.5 O.sub.2 F                                            335.4     2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   3'-methoxyphenoxy)-                                                            1-methyl-ethylamino]-s-triaz                                                   ine                              Prepara- tion Example 20                                                               ##STR41##                   C.sub.17 H.sub.24 N.sub.5 OF 333.4                                                       2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   3',4'-dimethyl- phenoxy)-1-m                                                   ethyl-ethylamino]- s-triazin                                                   e                                Prepara- tion Example 21                                                               ##STR42##                   C.sub.15 H.sub.19 N.sub.5 OF.sub.2                                             323.3     2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   3'-flurorphenoxy)- 1-methyl-                                                   ethylamino]-s-triazine           Prepara- tion Example 22                                                               ##STR43##                   C.sub.15 H.sub.19 N.sub.5 OF.sub.2                                             323.3     2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   2'-fluorophenoxy)- 1-methyl-                                                   ethylamino]-s-triazine           Prepara- tion Example 23                                                               ##STR44##                   C.sub.15 H.sub.19 N.sub.5 OF.sub.2                                             323.3     2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   4'-fluorophenoxy)- 1-methyl-                                                   ethylamino]-s-triazine           Prepara- tion Example 24                                                               ##STR45##                   C.sub.16 H.sub.18 N.sub.5 OF.sub.2                                             315.4     2-amino-4-[1-(benzofuran-2'-                                                    yl)ethylamino]-6-(α-f                                                   luoro, α- methyl                                                         ethyl)-s-triazine                Prepara- tion Example 25                                                               ##STR46##                   C.sub.16 H.sub.18 N.sub.5 OCl                                                            2-amino-4-[1-(benzofuran-2'-                                                    yl)ethylamino]-6-(α-c                                                   hloro, α- methyl                                                         ethyl)-s-triazine                Prepara- tion Example 26                                                               ##STR47##                   C.sub.16 H.sub.18 N.sub.5 OBr                                                            2-amino-4-[1-(benzofuran-2'-                                                    yl)ethylamino]-6-(α-b                                                   romo, α- methyl                                                          ethyl)-s-triazine                Prepara- tion Example 27                                                               ##STR48##                   C.sub.15 H.sub.16 N.sub.5 OF 301.3                                                       2-amino-4-[1-(benzofuran-2'-                                                    yl)ethylamino]-6-(α-f                                                   luoroethyl)- s-triazine          Prepara- tion Example 28                                                               ##STR49##                   C.sub.15 H.sub.16 N.sub.5 OCl                                                            2-amino-4-[1-(benzofuran-2'-                                                    yl)ethylamino]-6-(α-c                                                   hloroethyl)- s-triazine          Prepara- tion Example 29                                                               ##STR50##                   C.sub.17 H.sub.20 N.sub.5 OF 329.4                                                       2-amino-4-[1-(benzofuran-2-'                                                   - yl)ethylamino]-6-(α-                                                   fluoro, α- methyl                                                        propyl)-s-triazine               Prepara- tion Example 30                                                               ##STR51##                   C.sub.16 H.sub.18 N.sub.5 SF 331.4                                                       2-amino-4-[1-(benzothiophen-                                                    2'-yl)ethylamino]-6-(.alpha                                                   .-fluoro, α-methyl                                                       ethyl)-s-triazine                Prepara- tion Example 31                                                               ##STR52##                   C.sub.16 H.sub.18 N.sub.5 SCl                                                            2-amino-4-[1-(benzothiophen-                                                   2'- yl)ethylamino]-6-(.alpha                                                   .-chloro, α- methyl                                                      ethyl)-s-triazine                Prepara- tion Example 32                                                               ##STR53##                   C.sub.15 H.sub.16 N.sub.5 SF 317.4                                                       2-amino-4-[1-(benzothiophen-                                                   2'- yl)ethylamino]-6-(.alpha                                                   .-fluoroethyl)- s-triazine       Prepara- tion Example 33                                                               ##STR54##                   C.sub.17 H.sub.20 N.sub.5                                                                2-amino-4-[1-(6'-methylbenzo                                                   - furan-2'-yl)ethylamino]-6-                                                    (α-fluoro,                                                              α-methyl ethyl)-s-                                                       triazine                         Prepara- tion Example 34                                                               ##STR55##                   C.sub.16 H.sub.18 N.sub.5 OF 315.4                                                       2-amino-4-[1-(6'-methylbenzo                                                   furan- 2'-yl)ethylamino]-6-(                                                   α-fluoro- ethyl)-s-tri                                                   azine                            Prepara- tion Example 35                                                               ##STR56##                   C.sub.17 H.sub.20 N.sub.5 OCl                                                            2-amino-4-[1-6'-methylbenzof                                                   uran- 2'-yl)ethylamino]-6-(.                                                   alpha.-chloro, α-methy                                                   l ethyl)-s-triazine              Prepara- tion Example 36                                                               ##STR57##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                       2-amino-4-[α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   3'-methoxy,                                                                    4'- methylphenyl)-1-methyl-                                                    thylamino]-s-triazine            Prepara- tion Example 37                                                               ##STR58##                   C.sub.15 H.sub.20 N.sub.5 OF  305.4                                                      2-amino-4-(α-fluoroeth                                                   yl)-6- [2-(3'-methoxy,                                                         4'-methylphenyl)- 1-methyl-e                                                   thylamino]-s-triazine            Prepara- tion Example 38                                                               ##STR59##                   C.sub.16 H.sub.22 N.sub.5 OCl                                                            2-amino-4-(α-chloro,                                                     α-methyl)- 6-[2-(3'-me                                                   thoxy, 4'-methylphenyl)-                                                       1-methyl-ethylamino]-s-triaz                                                   ine                              Prepara- tion Example 39                                                               ##STR60##                   C.sub.16 H.sub.22 N.sub.5 OF 319.4                                                       2-amino-4-(α-fluoro,                                                     α-methyl ethyl)-6-[2-(                                                   3'-methyl,                                                                     4'- methoxyphenyl)-1-methyl-                                                    ethylamino]-s-triazine          Prepara- tion Example 40                                                               ##STR61##                   C.sub.15 H.sub.20 N.sub.5 OF 305.4                                                       2-amino-4-(α-fluoroeth                                                   yl)-6- [2-(3'-methyl,                                                          4'-methoxyphenyl)- 1-methyl-                                                   ethylamino]-s-triazine           Prepara- tion Example 41                                                               ##STR62##                   C.sub.16 H.sub.22 N.sub.5 OCl                                                            2-amino-4-(α-fluoro,                                                     α-methylethyl)- 6-[                                                      2-(3'-methyl,                                                                  4'-methoxyphenyl)- 1-methyl-                                                   ethylamino]-s-triazine           __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________     Preparation                                                                           Compound                                                                              Infrared absorption*.sup.1                                       Example No.                                                                           prepared                                                                              spectrum (cm.sup.-1)                                                                      Proton nuclear magnetic resonance                                              spectrum*.sup.2 (ppm)                                 __________________________________________________________________________      1     Compound 1                                                                            3470, 3350, 3280                                                                          1.35(3H, d), 1.65(6H, d), 2.28(6H, s),                                         3.91˜3.99(2H, m),                                             1660, 1620, 1560                                                                          4.25˜4.70(1H, brs), 5.44˜5.80(3H,                                  brs), 6.55˜6.60(3H, m)                                                   solvent: deuterated chloroform                         2     Compound 2                                                                            3500, 3440, 3200                                                                          1.33(3H, d), 1.60(3H, q), 2.26(6H, s),                                         3.90˜4.03(2H, m),                                             1660, 1620, 1560                                                                          4.30˜4.63(1H, brs), 4.80˜5.14(1H,                                  m), 5.38˜5.77(3H, m),                                                    6.52˜6.60(3H, m) solvent: deuterated                                     chloroform                                             3     Compound 3                                                                            3500, 3420, 3330                                                                          1.32(3H, d), 1.70(3H, d), 2.23(6H, s),                                         3.80˜4.18(2H, m),                                             1660, 1620, 1560                                                                          4.32˜4.80(3H, m), 6.50˜6.60(4H,                                    brs),                                                                          solvent: deuterated acetone                            4     Compound 4                                                                            3510, 3350, 3200                                                                          1.38(3H, d), 1.55(3H, d), 2.10(3H, s), 2.23(3H,                                s), 3.80˜                                                     1660, 1620, 1560                                                                          4.21(2H, m), 4.30˜4.78(2H, brs),                                         6.18˜7.42(6H, brs)                                                       solvent: deuterated acetone                            5     Compound 5                                                                            3470, 3350, 3250                                                                          1.37(3H, d), 1.63(6H, d), 2.17(3H, s), 2.30(3H,                                s), 3.96˜                                                     1658, 1586, 1540                                                                          4.00(2H, m), 4.32˜4.78(1H, brs),                                         5.26˜5.73(3H, brs),                                                      6.62˜7.35(3H, m) solvent: deuterated                                     chloroform                                             6     Compound 6                                                                            3530, 3360, 3250                                                                          1.40(3H, d), 1.88(6H, s), 2.19(3H, s), 2.31(3H,                                s), 3.96˜                                                     1650, 1580, 1575                                                                          4.03(2H, m), 4.32˜4.80(1H, brs),                                         5.32˜5.92(3H, brs),                                                      6.54˜7.22(3H, m) solvent: deuterated                                     chloroform                                             7     Compound 7                                                                            3500, 3350, 3200                                                                          1.39(3H, d), 1.88(6H, s), 2.16(3H, s), 2.27(3H,                                s), 3.91˜                                                     1650, 1590, 1560                                                                          4.01(2H, m), 4.28˜4.82(1H, brs),                                         5.28˜5.88(3H, brs),                                                      6.64˜7.29(3H, m) solvent: deuterated                                     chlorofrom                                             8     Compound 8                                                                            3530, 3360, 3220                                                                          1.38(3H, d), 1.62(3H, q), 2.14(3H, s), 2.28(3H,                                s), 3.95˜                                                     1660, 1580, 1560                                                                          4.00(2H, m), 4.32˜4.75(1H, brs),                                         4.87˜5.57(4H, brs),                                                      6.64˜7.20(3H, m) solvent: deuterated                                     chloroform                                             9     Compound 9                                                                            3460, 3350, 3200                                                                          1.35(3H, d), 1.89(6H, s), 2.30(6H, s),                                         3.88˜4.05(2H, m),                                             1660, 1620, 1550                                                                          4.24˜4.72(1H, brs), 5.16˜5.77(3H,                                  brs), 6.42˜6.79(3H, m)                                                   solvent: deuterated chloroform                        10     Compound 10                                                                           3500, 3360, 3200                                                                          1.37(3H, d), 2.08(6H, s), 2.29(6H, s),                                         3.84˜4.07(2H, m),                                             1640, 1600, 1560                                                                          4.26˜ 4.77(1H, brs), 5.08˜5.77(3H,                                 brs), 6.44˜6.75(3H, m)                                                   solvent: deuterated chloroform                        11     Compound 11                                                                           3530, 3360, 3200                                                                          1.37(3H, d), 1.63(6H, d), 3.93˜4.09(2H,                                  m), 4.27˜4.72                                                 1600, 1580, 1560                                                                          (1H, brs), 5.52˜6.60(3H, brs),                                           7.02˜7.48(4H, m)                                                         solvent: deuterated chloroform                        12     Compound 12                                                                           3440, 3330 1.36(3H, d), 1.64(6H, d), 2.32(3H, s),                                         3.94˜4.01(2H, m),                                             1650, 1610, 1570                                                                          4.29˜4.65(1H, brs), 5.28˜5.90(3H,                                  brs), 6.74˜7.17(4H, m)                                                   solvent: deuterated chloroform                        13     Compound 13                                                                           3500, 3340, 3190                                                                          1.36(3H, d), 1.62(3H, q), 2.32(3H, s),                                         3.94˜4.00(2H, m),                                             1640, 1620, 1564                                                                          4.19˜4.70(1H, brs), 4.96(1H, q),                                         5.17˜5.99(3H, brs),                                                      6.68˜7.24(4H, m) solvent: deuterated                                     chloroform                                            14     Compound 14                                                                           3500, 3350, 3200                                                                          1.36(3H, d), 1.62(3H, q), 3.98˜4.08(2H,                                  m), 4.29˜4.70                                                 1640, 1600, 1560                                                                          (1H, brs), 4.97(1H, q), 5.39˜6.50(3H,                                    brs)                                                                           solvent: deuterated chloroform                        15     Compound 15                                                                           3500, 3350, 3230                                                                          1.35(3H, d), 1.88(6H, s), 2.32(3H, s),                                         3.94˜4.01(2H, m),                                             1655, 1600, 1575                                                                          4.23˜4.77(1H, brs), 5.09˜5.99(3H,                                  brs), 6.68˜7.16(4H,m)                                                    solvent: deuterated chloroform                        16     Compound 16                                                                           3500, 3360, 3220                                                                          1.33(3H, d), 1.89(6H, s), 3.97˜4.04(2H,                                  m), 4.26˜ 4.76                                                1655, 1600, 1460                                                                          (1H, brs), 4.96˜5.73(3H, brs),                                           6.87˜7.38(5H, m)                                                         solvent: deuterated chloroform                        17     Compound 17                                                                           3500, 3380, 3180                                                                          1.34(3H, d), 1.63(6H, d), 3.93˜4.01(2H,                                  m), 4.18˜4.70                                                 1650, 1600, 1560                                                                          (1H, brs), 5.61˜5.58(3H, brs),                                           6.84˜7.36(5H, m)                                                         solvent: deuterated chloroform                        18     Compound 18                                                                           3510, 3350, 3200                                                                          1.34(3H, d), 1.60(3H, q), 3.88˜4.00(2H,                                  m), 4.25˜4.73                                                 1660, 1610, 1560                                                                          (1H, brs), 4.95(1H, q), 5.38˜6.62(3H,                                    brs), 6.83˜7.36                                                          (5H, m) solvent: deuterated chloroform                19     Compound 19                                                                           3470, 3380, 3220                                                                          1.36(3H, d), 1.64(6H, d), 3.79(3H, s),                                         3.91˜4.04(2H, m),                                             1650, 1610, 1575                                                                          4.28˜4.65(1H, brs), 5.32˜5.92(3H,                                  brs), 6.48˜7.17(4H, m)                                                   solvent: deuterated chloroform                        20     Compound 20                                                                           3440, 3330, 3200                                                                          1.33(3H, d), 1.62(6H, d), 2.17(3H, s), 2.21(3H,                                s), 3.89˜                                                     1650, 1595, 1560                                                                          3.96(2H, m), 4.20˜4.67(1H, brs),                                         5.48˜6.48(3H, brs),                                                      6.57˜7.12(3H, m) solvent: deuterated                                     chloroform                                            21     Compound 20                                                                           3440, 3330, 3240                                                                          1.35(3H, d), 1.64(6H, d), 3.93˜4.03(2H,                                  m), 4.26˜4.67                                                 1640, 1585, 1560                                                                          (1H, brs), 5.22˜5.92(3H, brs),                                           6.59˜7.37(4H, m)                                                         solvent: deuterated chloroform                        22     Compound 22                                                                           3500, 3320, 3240                                                                          1.39(3H, d), 1.64(6H, d), 4.01˜4.10(2H,                                  m), 4.29˜4.72                                                 1650, 1600, 1570                                                                          (1H, brs), 5.07˜5.74(3H, brs),                                           6.99˜7.02(4H, m)                                                         solvent: deuterated chloroform                        23     Compound 23                                                                           3520, 3350, 3220                                                                          1.36(3H, d), 1.64(6H, d), 3.91˜3.99(2H,                                  m), 4.23˜4.74                                                 1660, 1600, 1560                                                                          (1H, brs), 5.13˜5.68(3H, brs),                                           6.86˜6.98(4H, m)                                                         solvent: deuterated chloroform                        24     Compound 24                                                                           3500, 3310, 3220                                                                          1.56(6H, d), 1.65(3H, d), 5.30˜5.71(1H,                                  m), 6.20˜6.59                                                 1660, 1600, 1540                                                                          (2H, brs), 6.69(1H, s), 7.12˜7.64(4H, m)                                 solvent: deuterated acetone                           25     Compound 25                                                                           3490, 3340, 3270                                                                          1.62(3H, d), 1.89(6H, s), 5.25˜5.78(1H,                                  m), 6.57(1H, s),                                                    1640, 1610, 1560                                                                          7.11˜7.56(4H, m) solvent: deuterated                                     acetone                                               26     Compound 26                                                                           3490, 3350 1.63(3H, d), 2.07(6H, s), 5.24˜5.77(1H,                                  m), 6.57(1H, s),                                                    1650, 1580, 1560                                                                          7.16˜7.58(4H, m) solvent: deuterated                                     acetone                                               27     Compound 27                                                                           3490, 3320, 3190                                                                          1.60(3H, d, d), 1.61(3H, d), 4.90˜5.42(1H,                               q, q), 5.40˜6.08                                              1650, 1600, 1540                                                                          (1H, brs), 6.69(1H, s), 7.11˜7.56(4H, m)                                 solvent: deuterated acetone                           28     Compound 28                                                                           3490, 3320, 3220                                                                          1.57(3H, d), 1.72(3H, d), 4.69(1H, q),                                         5.24˜5.73(1H, m),                                             1660, 1600, 1560                                                                          6.69(1H, s), 7.08˜7.68(4H, m) solvent:                                   deuterated acetone                                    29     Compound 29                                                                           3460, 3320, 3180                                                                          1.20(3H, t), 1.57(3H, d), 1.65(3H, d), 1.88(1H,                                q), 5.16˜                                                     1650, 1590, 1540                                                                          6.00(4H, brs), 6.57(1H, s), 7.10˜7.56(4H,                                m)                                                                             solvent: deuterated acetone                           30     Compound 30                                                                           3540, 3290, 3150                                                                          1.61(6H, d), 1.62(3H, d), 5.31˜6.42(4H,                                  brs), 7.08˜7.83                                               1660, 1620, 1560                                                                          (5H, m) solvent: deuterated chloroform                31     Compound 31                                                                           3520, 3430, 3360                                                                          1.57(3H, d), 1.87(6H, s), 5.26˜6.33(4H,                                  brs), 6.99˜7.76                                               1650, 1570 (5H, m) solvent: deuterated chloroform                32     Compound 32                                                                           3500, 3430, 3330                                                                          1.53(3H, d,d), 1.62(3H, d), 4.69˜5.88(3H,                                brs), 6.20˜7.19                                               1650, 1570 (3H, brs), 7.21˜7.96(5H, m) solvent:                                     deuterated acetone                                    33     Compound 33                                                                           3510, 3430, 3350                                                                          1.58(6H, d), 1.62(3H, d), 2.41(3H, s),                                         5.22˜5.67(1H, m),                                             1660, 1570 6.28˜6.92(3H, brs), 6.61(1H, s),                                         6.92˜7.49(3H, m)                                                         solvent: deuterated acetone                           34     Compound 34                                                                           3490, 3430, 3330                                                                          1.60(3H, d,d), 1.62(3H, d), 2.42(3H, s),                                       4.72˜5.85(5H, brs),                                           1650, 1570 6.51(1H, s), 6.90˜7.49(3H, m) solvent:                                   deuterated chloroform                                 35     Compound 35                                                                           3500, 3430, 3350                                                                          1.62(3H, d), 1.89(6H, s), 2.43(3H, s),                                         5.08˜5.69(4H, brs),                                           1640, 1560 6.52(1H, s), 6.90˜7.49(3H, m)                                            solvent: deuterated chloroform                        36     Compound 36                                                                           3510, 3350, 3210                                                                          1.52(3H, d), 1.55(6H, d), 2.12(3H, s), 3.80(3H,                                s), 5.04˜                                                     1660, 1600, 1570                                                                          5.40(2H, m), 6.48(1H, brs), 6.78˜7.20(3H,                                m)                                                                             solvent: deuterated acetone                           37     Compound 37                                                                           3480, 3400, 3370                                                                          1.50(3H, d), 1.58(3H, d, d), 2.16(3H, s),                                      3.78(3H, s), 5.33˜                                            1670, 1620, 1560                                                                          6.34(4H, m), 6.78˜7.10(3H, m) solvent:                                   deuterated chloroform                                 38     Compound 38                                                                           3510, 3440, 3350                                                                          1.52(3H, d), 1.89(6H, s), 3.82(3H, s),                                         4.95˜5.67(4H, brs),                                           1650, 1570 6.76˜7.30(3H, m) solvent: deuterated                                     chloroform                                            39     Compound 39                                                                           3510, 3400, 3320                                                                          1.42(3H, d), 1.60(6H, d), 2.19(3H, s), 3.79(3H,                                s), 4.88˜                                                     1640, 1560 5.29(1H, m), 5.61˜7.20(3H, m)                                            solvent: deuterated chloroform                        40     Compound 40                                                                           3500, 3420, 3330                                                                          1.47(3H, d), 1.56(3H, d, d), 2.19(3H, s),                                      3.79(3H, s), 4.72˜                                            1650, 1570 6.57(5H, brs), 6.64˜7.28(3H, m)                                          solvent: deuterated chloroform                        41     Compound 41                                                                           3510, 3420, 3350                                                                          1.51(3H, d), 1.88(6H, s), 2.20(3H, s), 3.81(3H,                                s), 4.85˜                                                     1650, 1630, 1570                                                                          5.58(4H, brs), 6.69˜7.29(3H, m                                           solvent: deuterated chloroform                        __________________________________________________________________________      *.sup.1 KBr tablet method                                                      *.sup.2 Internal standard: tetramethyl silane                            

In the following, the actual method for form preparation is described by way of formulation examples. In the formulation examples given below, "parts" refers to % by weight.

Formulation Example 1: Water-dispersible powder

    ______________________________________                                         Compound of Preparation Example 1                                                                       20    parts                                           Diatomaceous earth       62    parts                                           White carbon             15    parts                                           Sodium alkylbenzene sulfonate                                                                           2     parts                                           Sodium lignin sulfonate  1     part                                            ______________________________________                                    

The above were blended and uniformly mixed and pulverized to give 100 parts of a water-dispersible powder.

Formulation Example 2: Emulsion

    ______________________________________                                         Compound of Preparation Example 2                                                                       40 parts                                              Xylene                   20 parts                                              Dimethyl formamide       20 parts                                              Solpol 2806B (surface active agent,                                                                     20 parts                                              manufactured by Toho Chemical                                                  Industry)                                                                      ______________________________________                                    

The above were uniformly dissolved and mixed to give 100 parts of an emulsion.

Formulation Example 3: Dust

    ______________________________________                                         Compound of Preparation Example 3                                                                       2 parts                                               Diatomaceous earth       20 parts                                              Talc                     78 parts                                              ______________________________________                                    

The above were blended and uniformly mixed and pulverized to give 100 parts of a dust.

Formulation Example 4: Granules

    ______________________________________                                         Compound of Preparation Example 4                                                                       1     part                                            Bentonite                30    parts                                           Talc                     66    parts                                           Sodium lignin sulfonate  3     parts                                           ______________________________________                                    

The above were blended, uniformly mixed and pulverized and thoroughly kneaded with addition of water followed by granulation and drying to give 100 parts of granules.

Formulation Example 5: Flowable agent

    ______________________________________                                         Compound of Preparation Example 5                                                                       25     parts                                          Methyl cellulose         0.3    part                                           Colloidal silica         1.5    parts                                          Sodium lignin sulfonate  1      part                                           Polyoxyethylene nonylphenyl ether                                                                       2      parts                                          Water                    70.2   parts                                          ______________________________________                                    

The above were thoroughly mixed and dispersed and the slurry-like mixture was subjected to wet-process pulverization to give 100 parts of a stable flowable agent.

Formulation Example 6: Water-dispersible Powder

A carrier for water-dispersible powder was obtained by uniformly pulverizing and mixing 97 parts of clay (commercial product name: Zieglite, manufactured by Zieglite Kogyo) as a carrier, 1.5 parts of an alkylaryl sulfonic acid salt (commercial product name: Neopelex, manufactured by Kao Atlas Co.) as a surface active agent and 1.5 parts of a non-ionic type and anionic type surface active agent (commercial product name: Solpol 800A, manufactured by Toho Chemical Industry Co.).

A water-dispersible powder was obtained by uniformly pulverizing and mixing 90 parts of this carrier for water-dispersible powder and 10 parts of the triazine derivative obtained in the above described Preparation Examples 1 to 5.

EXAMPLES 1 TO 41 UPLAND FIELD SOIL TREATMENT TEST

Wagner pots of 1/2000 were filled with a soil of non-paddy field and seeds of Digitaria sanguinalis, Alopecurus myosuroides, Abutilon theophrasti, Veronica persica, Viola arvensis, Polygonum persicaria, Amaranthus patulus, Galium sparium var. echinospermon, wheat, barley, corn and grain sorghum were uniformly sowed in the surface layer.

Prior to the germination of the wheat, barley, corn, grain sorghum and weeds thereafter, the soil surface was uniformly treated with a specified volume of a diluted solution of the herbicide obtained in the above described Formulation Example 6 and the pots were kept standing in a greenhouse with periodical water sprinkling.

Table 4 shows the results of the investigations of the herbicidal effects and phytotoxicity to the wheat, barley, corn and grain sorghum after 30 days from the treatment with the herbicide solution. The dose was 25 to 100 g/10 ares calculated as the amount of the effective ingredient. The phytotoxicity to the wheat, barley, corn and grain sorghum and the herbicidal effects are expressed as shown below by measuring the respective air-dried weights.

    ______________________________________                                                         Phytotoxicity to wheat, barley,                                                corn & grain sorgham (relative                                 Extent of phytotoxicity                                                                        to untreated zone)                                             ______________________________________                                         0               100%                                                           1               61 to 99%                                                      2               21 to 60%                                                      3               11 to 20%                                                      4               1 to 10%                                                       5               0%                                                             ______________________________________                                                         Herbicidal effects                                             Degree of herbi-                                                                               (relative to un-                                               cidal effects   treated zone)                                                  ______________________________________                                         0               100%                                                           1               61 to 99%                                                      2               21 to 60%                                                      3               11 to 20%                                                      4               1 to 10%                                                       5               0%                                                             ______________________________________                                    

COMPARATIVE EXAMPLES 1 TO 6

The same procedure as in Example 1 was undertaken excepting the use of the triazine derivatives A to C (described in the official publication of Japanese Patent Kokai No. 63-264465), D (described in the official publication of Japanese Patent Kokai No..63-51379), E (described in the official publication of Japanese Patent Kokai No. 63-146876) or F (described in the official publication of Japanese Patent Toku-Sai-Hyo No. 88/02368) expressed by the formulas given below in place of the triazine derivative prepared in Preparation Example 1, in Example 1. The results are shown in Table 4. ##STR63##

                                      TABLE 4                                      __________________________________________________________________________                   Herbicidal effect                                                              Alope-                        Galium                                      Amount                                                                              curus             Poly-       sparium                                                                             Phytotoxicity                     Com- of herb-                                                                            myo-                                                                               Digitaria                                                                           Abutilon                                                                            Ver-                                                                               gonum                                                                              Viola                                                                              Amar-                                                                              var.           Grain                   pound                                                                               icide                                                                               sur-                                                                               san- theo-                                                                               onica                                                                              persi-                                                                             arven-                                                                             anthus                                                                             echino-  Bar-  sor                 No. used (g/10a)                                                                             oides                                                                              guinalis                                                                            phrasti                                                                             persica                                                                            caria                                                                              sis patulus                                                                            spermon                                                                             Wheat                                                                              ley                                                                               Corn                                                                              ghum                __________________________________________________________________________     Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   1   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 1                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   2   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 2                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   3   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 3                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   4   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 4                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   5   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 5                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   6   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 6                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   7   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 7                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   8   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 8                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   9   Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 9                                                                    Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   10  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 10                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   11  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 11                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   12  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 12                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   13  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 13                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   14  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 14                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   15  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 15                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   16  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 16                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   17  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 17                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   18  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 18                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   19  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 19                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   20  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 20                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   21  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 21                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   22  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 22                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   23  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 23                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   24  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 24                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   25  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 25                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   26  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 26                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   27  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 27                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   28  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 28                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   29  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 29                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   30  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 30                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   31  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 31                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   32  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 32                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   33  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 33                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   34  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 34                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   35  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 35                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   36  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 36                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   37  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 37                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   38  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 38                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   39  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 39                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   40  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 40                                                                   Ex- Com- 100  5   5    5    5   5   5   5   5    0   0  0  0                   ample                                                                              pound of                                                                            50   5   5    5    5   5   5   5   5    0   0  0  0                   41  Prepara-                                                                            25   5   5    5    5   5   5   5   5    0   0  0  0                       tion Ex-                                                                       ample 41                                                                   Com-                                                                               Triazine                                                                            100  4   5    4    5   5   4   5   4    0   0  0  0                   para-                                                                              deriva-                                                                             50   3   3    4    4   3   3   3   2    0   0  0  0                   tive                                                                               tive A                                                                              25   1   1    2    3   2   2   1   1    0   0  0  0                   Ex-                                                                            ample                                                                          Com-                                                                               Triazine                                                                            100  3   3    4    4   3   3   4   2    0   0  0  0                   para-                                                                              deriva-                                                                             50   1   1    3    3   2   2   3   0    0   0  0  0                   tive                                                                               tive B                                                                              25   0   0    1    1   1   0   1   0    0   0  0  0                   Ex-                                                                            ample                                                                          2                                                                              Com-                                                                               Triazine                                                                            100  5   5    4    5   5   5   5   3    0   0  0  0                   para-                                                                              deriva-                                                                             50   3   3    4    4   4   4   3   1    0   0  0  0                   tive                                                                               tive C                                                                              25   2   2    3    3   2   2   2   1    0   0  0  0                   Ex-                                                                            ample                                                                          3                                                                              Com-                                                                               Triazine                                                                            100  5   5    4    5   5   4   5   4    0   0  0  0                   para-                                                                              deriva-                                                                             50   3   3    4    4   4   4   4   3    0   0  0  0                   tive                                                                               tive D                                                                              25   3   2    3    3   3   3   3   1    0   0  0  0                   Ex-                                                                            ample                                                                          4                                                                              Com-                                                                               Triazine                                                                            100  3   4    4    3   3   4   4   2    0   0  0  0                   para-                                                                              deriva-                                                                             50   1   2    3    3   3   2   2   0    0   0  0  0                   tive                                                                               tive E                                                                              25   0   0    1    0   0   0   0   0    0   0  0  0                   Ex-                                                                            ample                                                                          5                                                                              Com-                                                                               Triazine                                                                            100  3   5    4    5   4   4   5   4    0   0  0  0                   para-                                                                              deriva-                                                                             50   2   3    3    4   3   4   3   3    0   0  0  0                   tive                                                                               tive F                                                                              25   0   1    2    2   1   2   0   1    0   0  0  0                   Ex-                                                                            ample                                                                          6                                                                              __________________________________________________________________________

EXAMPLES 42 TO 82 FOLIAGE TREATMENT TEST

Seeds of weeds including Abutilon theophrasti, Common blackjack, Amaranthus patulus, Cassia obtusifolia, Ipomoea purpurea, Galium sparium var. echinospermon, Veronica persica and seeds of crops including corn, grain sorghum, wheat, barley and oat were sowed on to the Wagner pots of 1/2000 filled with soil of upland field and, after covering up with soil, were grown in a greenhouse and, when the weeds were in their mono- to bi-foliate period and the crops were in their tri-foliate period, an aqueous suspension of a specified amount of the herbicide prepared in the above described Formulation Example 6 was uniformly sprinkled by spraying to the parts of stems and leaves in a liquid volume corresponding to 100 liters/10 ares. Thereafter, they were grown in a greenhouse and the phytotoxicity on the crops and the herbicidal effects were estimated according to the following criteria on the 20th day of the treatment. The results are shown in Table 5.

                  TABLE 5                                                          ______________________________________                                         [Criteria of estimation]                                                       Degree of herbicidal                                                                          Herbicidal effects                                              effects        (% killed weeds)                                                ______________________________________                                         0              less than 5%                                                                   (almost no effects)                                             1               5 to 20%                                                       2              20 to 40%                                                       3              40 to 70%                                                       4              70 to 80%                                                       5              90% or more                                                                    (almost complete withering)                                     ______________________________________                                    

The % killed weeds given above was obtained from the following equation by determining the overground raw grass weight in the phytotoxicity treated zone and the overground raw grass weight in the untreated zone. ##EQU1##

COMPARATIVE EXAMPLES 7 TO 12

The same procedure as in Example 6 was undertaken excepting the use of the triazine derivative A, B, C, D, E or F shown in Comparative Examples 1 to 6 in place of the triazine derivative prepared in Preparation Example 1, in Example 42. The results are shown in Table 5.

    TABLE 5       Herbicidal effect      Galium  Amount of Phytotoxicity  Cassia  sparium       Compound herbicide  Grain    Abutilon Common Amaranthus obtusifolia      Ipomoea var. Veronica No. used (g/10a) Corn sorghum Wheat Barley Oats      theophrasti blackjack patulus L. purpurea echinospermon persica        Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 42 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  1 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 43 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  2 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 44 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  3 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 45 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  4 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 46 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  5 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 47 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  6 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 48 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  7 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 49 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  8 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 50 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  9 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 51 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  10 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 52 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  11 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 53 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  12 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 54 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  13 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 55 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  14 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 56 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  15 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 57 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  16 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 58 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  17 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 59 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  18 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 60 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  19 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 61 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  20 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 62 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  21 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 63 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  22 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 64 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  23 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 65 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  24 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 66 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  25 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 67 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  26 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 68 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  27 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 69 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  28 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 70 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  29 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 71 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  30 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 72 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  31 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 73 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  32 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 74 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  33 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 75 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  34 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 76 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  35 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 77 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  36 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 78 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  37 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 79 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  38 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 80 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  39 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 81 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  40 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Example Compound 400 0 0 0 0 0 5 5 5 5 5 5 5 82 of 200 0 0 0 0 0 5 5 5      5 5 5 5  Prepara- 100 0 0 0 0 0 5 5 5 5 5 5 5  tion 50 0 0 0 0 0 5 5 5 5      5 5 5  Example 25 0 0 0 0 0 5 5 5 5 5 5 5  41 12.5 0 0 0 0 0 5 5 5 5 5 5      5 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0 0      0 5 5 5 5 5 5 5 Example tive B 100 0 0 0 0 0 5 5 5 5 5 5 5 7  50 0 0 0 0      0 5 3 4 3 3 3 4   25 0 0 0 0 0 3 3 4 3 3 2 3   12.5 0 0 0 0 0 1 2 2 2 2      1 2 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0 0      0 0 5 5 5 5 5 5 5 Example tive C 100 0 0 0 0 0 5 5 5 5 5 5 5 8  50 0 0 0      0 0 3 3 4 4 3 3 4   25 0 0 0 0 0 3 3 4 2 3 2 3   12.5 0 0 0 0 0 2 2 2 1      2 1 2 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0 0      0 0 0 5 5 5 5 5 5 5 Example tive D 100 0 0 0 0 0 5 5 5 5 5 5 5 9  50 0 0      0 0 0 5 5 5 5 4 5 5   25 0 0 0 0 0 4 4 4 4 3 4 4   12.5 0 0 0 0 0 2 2 2      2 3 3 3 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva- 200 0      0 0 0 0 5 5 5 5 5 5 5 Example tive E 100 0 0 0 0 0 5 5 5 5 5 4 5 10  50      0 0 0 0 0 4 4 5 5 5 4 3   25 0 0 0 0 0 4 4 4 3 4 3 2   12.5 0 0 0 0 0 3      3 4 2 3 2 1 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive deriva-      200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive F 100 0 0 0 0 0 5 5 5 4 5 5 5      11  50 0 0 0 0 0 3 5 5 3 5 3 4   25 0 0 0 0 0 3 5 5 2 5 2 3   12.5 0 0 0      0 0 1 4 5 2 3 1 2 Compara- Triazine 400 0 0 0 0 0 5 5 5 5 5 5 5 tive      deriva- 200 0 0 0 0 0 5 5 5 5 5 5 5 Example tive G 100 0 0 0 0 0 5 5 5 5      5 5 5 12  50 0 0 0 0 0 4 5 5 4 5 5 5   25 0 0 0 0 0 3 5 5 3 5 4 4   12.5      0 0 0 0 0 1 4 5 2 3 3 3

EXAMPLES 83 TO 123: PADDY SOIL TREATMENT TEST

Porcelain pots of 1/15500 are were filled with a paddy field soil and seeds of Echinochola crus-galli P. Beauv.var formosenis Ohwi, Cyperus difformis L., broad-leaved weeds (Rotala indica (Willd) Koehne var. uligirosa (Miq.) Koehne and Monochoria vaginalis Presl var. plantaginea) and Scirpus juncoides Roxb. ssp. Hotarui Ohwi T. Koyama were uniformly sowed to the surface layer and further tubers of Cyperus serotinus Rottb. and Sagittaria pygmaea Miq. were transplanted followed by transplantation of paddy rice in the bifoliate period.

Before germination of the weeds, thereafter, a specified volume of a diluted solution of the herbicide obtained in the above described Formulation Example 6 was uniformly dropped to the water surface to effect treatment followed by standing of the pots in a greenhouse with periodical sprinkling of water.

Table 6 shows the results in the investigations of the herbicidal effects and phytotoxicity to the rice crop after 20 days from the treatment with the herbicide solution. Incidentally, dose is given by the amount of the effective ingredient per 10 ares. And, the phytotoxicity to paddy rice and the herbicidal effects are expressed as shown below by determining the respective air-dried weights.

    ______________________________________                                                         Phytotoxicity to paddy rice                                    Extent of phytotoxicity                                                                        (relative to untreated zone)                                   ______________________________________                                         0               100%                                                           1               95 to 99%                                                      2               90 to 94%                                                      3               80 to 89%                                                      4               60 to 79%                                                      5               50 to 59%                                                      ______________________________________                                         Degree of herbi-                                                                               Herbicidal effects (relative                                   cidal effects   to untreated zone)                                             ______________________________________                                         0               100%                                                           1               61 to 99%                                                      2               21 to 60%                                                      3               11 to 20%                                                      4                1 to 10%                                                      5                0%                                                            ______________________________________                                    

COMPARATIVE EXAMPLES 13 TO 18

The same procedure as in Example 11 was undertaken excepting the use of the triazine derivative A, B, C, D, E or F shown in Comparative Examples 1 to 6 in place of the triazine derivative prepared in Preparation Example 1, in Example 83. The results are shown in Table 6.

                                      TABLE 6                                      __________________________________________________________________________                 Amount                                                                              Herbicidal effect                                                         of   Echinochola crus-galli                                                                    Cyperus                                                                             Scirpus juncoides                                                                        Cyperus    Sagittaria                                                                          Paddy                     Compound                                                                             herbicide                                                                           P. Beauv. var.                                                                            serotinus                                                                           Roxb. ssp. Hotarui                                                                       difformis                                                                           Broadleaf                                                                            pygmaea                                                                             rice                No.   used  (g/10a)                                                                             formosensis Ohwi                                                                          Rottb.                                                                              Ohwi T. Koyama                                                                           L.   weeds Miq. plants              __________________________________________________________________________     Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   83    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 1                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   84    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 2                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   85    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 3                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   86    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 4                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   87    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 5                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   88    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 6                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   89    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 7                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   90    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 8                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   91    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 9                                                                            12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   92    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 10                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   93    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 11                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   94    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 12                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   95    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 13                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   96    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 14                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   97    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 15                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   98    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 16                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   99    of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 17                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   100   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 18                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   101   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 19                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   102   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 20                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   103   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 21                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   104   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 22                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   105   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 23                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   106   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 24                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   107   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 25                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   108   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 26                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   109   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 27                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   110   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 28                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   111   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 29                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   112   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 30                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   113   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 31                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   114   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 32                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   115   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 33                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   116   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 34                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   117   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 35                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   118   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 36                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   119   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 37                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   120   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 38                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   121   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 39                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   122   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 40                                                                           12.5 5          5    5         5    5     5    0                   Example                                                                              Compound                                                                             100  5          5    5         5    5     5    0                   123   of    50   5          5    5         5    5     5    0                         Preparation                                                                          25   5          5    5         5    5     5    0                         Example 41                                                                           12.5 5          5    5         5    5     5    0                   Compara-                                                                             Triazine                                                                             100  5          5    5         5    5     5    0                   tive  derivative                                                                           50   5          5    4         5    4     5    0                   Example                                                                              A     25   5          4    3         5    4     3    0                   13          12.5 5          4    2         5    4     2    0                   Compara-                                                                             Triazine                                                                             100  5          4    5         5    5     5    0                   tive  derivative                                                                           50   5          4    5         5    4     5    0                   Example                                                                              B     25   5          3    4         5    4     3    0                   14          12.5 5          3    2         5    4     2    0                   Compara-                                                                             Triazine                                                                             100  5          5    5         5    5     5    0                   tive  derivative                                                                           50   5          5    5         5    5     5    0                   Example                                                                              C     25   5          5    3         5    5     3    0                   15          12.5 5          3    2         5    5     3    0                   Compara-                                                                             Triazine                                                                             100  5          5    5         5    5     5    0                   tive  derivative                                                                           50   5          5    5         5    5     5    0                   Example                                                                              D     25   5          5    5         5    5     5    0                   16          12.5 5          5    3         5    5     3    0                   Compara-                                                                             Triazine                                                                             100  5          5    5         5    5     5    0                   tive  derivative                                                                           50   5          5    5         5    5     5    0                   Example                                                                              E     25   5          5    5         5    5     5    0                   17          12.5 5          4    3         5    5     3    0                   Compara-                                                                             Triazine                                                                             100  5          5    5         5    5     5    0                   tive  derivative                                                                           50   5          5    5         5    5     5    0                   Example                                                                              F     25   5          5    5         5    5     5    0                   18          12.5 5          3    4         5    5     3    0                   __________________________________________________________________________

Utilizability in industry

The triazine derivative of the present invention is a novel compound and can be efficiently utilized as a herbicide. The herbicide of the present invention with the said triazine derivative as the effective ingredient exhibits, as compared with conventional herticides for upland field, excellent herbicidal effects against weeds including troublesome weeds without causing phytotoxicity to upland crops and, in particular, a remarkably high effect can be obtained by the treatment to the soil before preemergence or by the treatment to foliage in the fields of crops belonging to Gramineous crops. Further, the herbicides of the present invention exhibit higher effectiveness against troublesome weeds still with less phytotoxicity than hitherto known herbicides for paddy rice. 

We claim:
 1. A triazine compound of the formula ##STR64## wherein A is ##STR65## in which Y² and Y³ are the same or different and each is a methyl group or a methoxy group or ##STR66## in which Y⁴ is a methyl group, a trifluoromethyl group, a methoxy group or a fluorine atom and n is an integer of 0 to 2,X¹ is a halogen atom and R¹ is hydrogen, a methyl group or an ethyl group.
 2. The triazine compound of claim 1, wherein A is said ##STR67##
 3. The triazine compound of claim 2, wherein Y⁴ is a methyl group.
 4. The triazine compound of claim 1, wherein A is said ##STR68##
 5. The triazine compound of claim 1, wherein the compound is selected from the group consisting of2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-bromo, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-(2-phenoxy-1-methylethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-(2-phenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxyphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3',4'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(4'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl)-6-[2-(3'-methoxy, 4-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, and 2-amino-4-(α-fluoro, α-methylethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine.
 6. A herbicidal composition comprising an effective herbicidal amount of a triazine compound of claim 1 in admixture with a carrier.
 7. A herbicidal composition according to claim 6, wherein the triazine compound is selected from the group consisting of2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-bromo, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-phenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxyphenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-(2-(3',4'-dimethylphenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(4'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-[α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, and 2-amino-4-(α-fluoro, α-methylethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine.
 8. A method of combatting weeds comprising applying to weeds or to a locus thereof an effective herbicidal amount of a triazine compound of claim
 1. 9. The method of combatting weeds according to claim 8, wherein the triazine compound is selected from the group consisting of2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(2',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(2',3'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-bromo, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-trifluoromethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-[2-(3'-methylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl ethyl)-6-(2-phenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-(2-phenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-(2-phenoxy-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxyphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3',4'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(2'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(4'-fluorophenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-chloro, α-methyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine, and 2-amino-4-(α-fluoro, α-methylethyl)-6-[2-(3'-methyl, 4'-methoxyphenyl)-1-methyl-ethylamino]-s-triazine.
 10. The triazine compound of claim 3, wherein X¹ is a fluorine atom or a chlorine atom, R¹ is hydrogen or a methyl group and n is
 2. 11. The method of combatting weeds according to claim 8, wherein the triazine compound is of the formula ##STR69## Y⁴ is a methyl group, R¹ is a hydrogen or a methyl group andn is
 2. 12. The method of combatting weeds according to claim 11, wherein said triazine compound is applied to a soil surface in an amount of 1 g/10 ares to 100 g/10 ares.
 13. The triazine compound of claim 10, wherein the compound is selected from the group consisting of2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine and 2-amino-4-(α-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine.
 14. The method of combatting weeds according to claim 8, wherein said triazine compound is applied to a soil surface in an amount of 1 g/10 ares to 100 g/10 ares.
 15. The method of combatting weeds according to claim 8, wherein the weeds are selected from the group consisting of Alopercurus myosuroides, Digitaria sanguinalis, Abutilon theophrasti, Veronica persica, Polygonum persicaria, Viola arvensis, Amaranthus patulus and Galium sparium var. echinospermon.
 16. The method of combatting weeds according to claim 9, wherein said triazine compound is applied to a soil surface in an amount of 1 g/10 ares to 100 g/10 ares and the weeds are selected from the group consisting of Alopercurus myosuroides, Digitaria sanguinalis, Abutilon theophrasti, Veronica persica, Polygonum persicaria, Viola arvensis, Amaranthus patulus and Galium sparium var. echinospermon.
 17. The method of combatting weeds according to claim 16, wherein the triazine compound is selected from the group consisting of2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine, 2-amino-4-(α-fluoroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine and 2-amino-4-(α-chloroethyl)-6-[2-(3',5'-dimethylphenoxy)-1-methyl-ethylamino]-s-triazine.
 18. The triazine compound of claim 1, wherein X¹ is a fluorine atom or a chlorine atom, R¹ is hydrogen or a methyl group.
 19. The triazine compound of claim 18, wherein the compound is selected from the group consisting of2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine and 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine.
 20. The method of combatting weeds according to claim 16, wherein the triazine compound is selected from the group consisting of2-amino-4-(α-fluoro, α-methyl ethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine and 2-amino-4-(α-fluoroethyl)-6-[2-(3'-methoxy, 4'-methylphenyl)-1-methyl-ethylamino]-s-triazine. 